Phenylhydrazine → HCID 45377374, compound

HRID 1962417Notes

Reaction equation

[C:1]([C:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7](=[O:14])[O:6][C:5]=1[NH:15][C@H:16]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[CH2:17][CH3:18])(=O)[CH3:2].[C:25]1([NH:31][NH2:32])[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>C(#N)C>[C:19]1([C@@H:16]([NH:15][C:5]([C:4]2[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[C:7](=[O:14])[N:32]([NH:31][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[C:1]=2[CH3:2])=[O:6])[CH2:17][CH3:18])[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

Conditions

Temperature: 160 °C

Procedure

A mixture of 4-acetyl-3-((S)-1-phenyl-propylamino)-isochromen-1-one (60 mg) and phenylhydrazine (28 mg, 0.259 mmol) in acetonitrile (0.5 mL) was heated under microwave irradiation at 160° C. for 15 min and evaporated. The title compound was separated by flash chromatography on SiO2 (20 g, gradient heptane-ethyl acetate, the product came out with 50% ethyl acetate) to give 51 mg of a white solid, yield 66%. LC-MS (m/z) 412.2 (MH+); tR=1.48. 1H NMR (250 MHz, 70° C., DMSO-d6): 0.97 (t, J=7.3 Hz, 3H, Me of Et), 1.75-1.94 (m, 3H, CH2 of Et), 2.25 (s, 3H, Me), 4.98 (q (unresolved dt), J(d)=7 Hz, J(0=8.1 Hz, 1H, CH—NH), 6.68 (d, J=7.9 Hz, 2H, PhN), 6.83 (t, J=7.3 Hz, 1H, PhN), 7.14-7.51 (m, 9H), 7.69 (unres dt, J(t)=7.7 Hz, J(d)=1 Hz, 1H), 8.75 (s, 1H, NHPh), 8.8 (br. d, J=8.3 Hz, NHCO).

Workup

customevaporated
customThe title compound was separated by flash chromatography on SiO2 (20 g, gradient heptane-ethyl acetate

Sources & evidence

ORD record: ord-57064531d4204a8bbfb8c99ff7b6cf5c
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08415373B2

Reaction notes

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